Structural and spectral speciation on methyl 2-(3-(furan-2-carbonyl)thioureido)benzoate: A comparative experimental and theoretical study

Singh, Durga P.; Pratap, Seema; Gupta, Sushil K.; Butcher, Ray J.

doi:10.1016/j.molstruc.2013.05.059

Cited by 8 publications

(4 citation statements)

References 60 publications

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“…The m s (NCN) stretching mode is usually assigned to the thioamide band III. For the thiourea molecule [55], the symmetric motion of the CAN stretching occurs at around 1150 cm À1 [56,57]. In the present case, following the quantum chemical calculation description, the m s (NCN) modes of 1 and 2 are assigned to the 1152 (1160) and 1160 (1158) cm À1 intense absorptions found in the infrared (Raman values in parentheses) spectra, respectively, also in agreement with previous work on similar species [58].…”

Section: Vibrational Analysissupporting

confidence: 89%

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Saeed

Ashraf

White

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Two novel 1-(1-naphthoyl)-3-(halo-phenyl) substituted thioureas, namely 1-(1-naphthoyl)-3-(2,4-di-fluoro-phenyl)-thiourea (1) and 1-(1-naphthoyl)-3-(3-chloro-4-fluoro-phenyl)-thiourea (2), were synthesized and fully characterized. The X-ray crystal and molecular structures have been determined resulting in a planar acylthiourea group, with the C=O and C=S adopting a pseudo-antiperiplanar conformation. An intramolecular N-H⋯O=C hydrogen bond occurs between the thioamide and carbonyl groups. The crystal packing of both compounds is characterized by extended intermolecular N-H⋯S=C and N-H⋯O=C hydrogen-bonding interactions involving the acylthiourea moiety. Compound 2 is further stabilized by π-stacking between adjacent naphthalene and phenyl rings. The thermal behavior, as well as the vibrational properties, studied by infrared and Raman spectroscopy data complemented by quantum chemical calculations at the B3PW91/6-311++G(d,p) support the formation of these intra- and intermolecular hydrogen bonds. Furthermore, the UV-Vis spectrum is interpreted in terms of TD-DFT quantum chemical calculations with the shapes of the simulated absorption spectra in good accordance with the experimental data.

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Section: Vibrational Analysissupporting

confidence: 89%

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Saeed

Ashraf

White

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Interactions between the grafted ligands and the metal ions are obvious based on the change in position and intensity for the various bands according to FT-IR spectroscopy (Figure ). In general, the larger the shift and/or the intensity of the IR band upon metal adsorption, the higher is the affinity of the ligand toward the analyzed metals, i.e., stronger and more favorable are the ligand–metal interactions. , For KIT-6-N-FDGA, the FT-IR spectrum confirms the existence of the amide group, i.e., the band at about 1660 cm –1 (amide I band; CO stretching), the band at 1577 cm –1 (amide II band; NH deformation, CN stretching), and bands related to CC stretching and ring-stretching vibration at about 1640 (shoulder) and 1600 cm –1 , and 1525 cm –1 , respectively (Figure a). − After metal loading, all the samples show a lower intensity of the OH band (3740 cm –1 ), as compared to the pristine sorbent. The Fe-containing sample does not show any shift of the amide I band (1660 cm –1 ).…”

Section: Results and Discussionmentioning

confidence: 86%

“… 62 , 63 For KIT-6-N-FDGA, the FT-IR spectrum confirms the existence of the amide group, i.e., the band at about 1660 cm –1 (amide I band; C=O stretching), the band at 1577 cm –1 (amide II band; NH deformation, CN stretching), and bands related to C=C stretching and ring-stretching vibration at about 1640 (shoulder) and 1600 cm –1 , and 1525 cm –1 , respectively ( Figure 10 a). 52 − 55 After metal loading, all the samples show a lower intensity of the OH band (3740 cm –1 ), as compared to the pristine sorbent. The Fe-containing sample does not show any shift of the amide I band (1660 cm –1 ).…”

Section: Results and Discussionmentioning

confidence: 95%

Understanding Selectivity of Mesoporous Silica-Grafted Diglycolamide-Type Ligands in the Solid-Phase Extraction of Rare Earths

Florek

Larivière

Kählig

et al. 2020

ACS Appl. Mater. Interfaces

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Rare earth elements (REEs) and their compounds are essential for rapidly developing modern technologies. These materials are especially critical in the area of green/sustainable energy; however, only very high-purity fractions are appropriate for these applications. Yet, achieving efficient REE separation and purification in an economically and environmentally effective way remains a challenge. Moreover, current extraction technologies often generate large amounts of undesirable wastes. In that perspective, the development of selective, reusable, and extremely efficient sorbents is needed. Among numerous ligands used in the liquid–liquid extraction (LLE) process, the diglycolamide-based (DGA) ligands play a leading role. Although these ligands display notable extraction performance in the liquid phase, their extractive chemistry is not widely studied when such ligands are tethered to a solid support. A detailed understanding of the relationship between chemical structure and function (i.e., extraction selectivity) at the molecular level is still missing although it is a key factor for the development of advanced sorbents with tailored selectivity. Herein, a series of functionalized mesoporous silica (KIT-6) solid phases were investigated as sorbents for the selective extraction of REEs. To better understand the extraction behavior of these sorbents, different spectroscopic techniques (solid-state NMR, X-ray photoelectron spectroscopy, XPS, and Fourier transform infrared spectroscopy, FT-IR) were implemented. The obtained spectroscopic results provide useful insights into the chemical environment and reactivity of the chelating ligand anchored on the KIT-6 support. Furthermore, it can be suggested that depending on the extracted metal and/or structure of the ligand and its attachment to KIT-6, different functional groups (i.e., C=O, N–H, or silanols) act as the main adsorption centers and preferentially capture targeted elements, which in turn may be associated with the different selectivity of the synthesized sorbents. Thus, by determining how metals interact with different supports, we aim to better understand the solid-phase extraction process of hybrid (organo)silica sorbents and design better extraction materials.

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“…Taking into account the vibrational properties reported for the simple thiourea molecule [63], it is expected that the corresponding symmetric motion of the CAN stretching modes at around 1150 cm À1 [64,65]. Thus, following the quantum chemical calculation description, the m s (NCN) symmetric stretching modes (usually assigned as thioamide band III), are assigned to the 1153 (1146) and 1150 (1143) cm À1 intense absorptions found in the infrared spectra of 1 and 2 and to the 1176 cm À1 (1171 cm À1 ) band for 3 (Raman values are given in parentheses).…”

Section: Vibrational Analysismentioning

confidence: 99%

The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

Saeed

Flörke

Erben

2014

Journal of Molecular Structure

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Structural and spectral speciation on methyl 2-(3-(furan-2-carbonyl)thioureido)benzoate: A comparative experimental and theoretical study

Cited by 8 publications

References 60 publications

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Synthesis, X-ray crystal structure, thermal behavior and spectroscopic analysis of 1-(1-naphthoyl)-3-(halo-phenyl)-thioureas complemented with quantum chemical calculations

Understanding Selectivity of Mesoporous Silica-Grafted Diglycolamide-Type Ligands in the Solid-Phase Extraction of Rare Earths

The role of substituents in the molecular and crystal structure of 1-(adamantane-1-carbonyl)-3-(mono)- and 3,3-(di) substituted thioureas

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